# US 10,864,281 B2 · Inclusion complexes and methods for making the same

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- Number: US 10,864,281 B2
- Document ID: US10864281B2
- Status: Granted
- Kind: B2
- Application number: 16/145,416
- Filed: 2018-09-28
- Published: 2019-04-04
- Granted: 2020-12-15
- Earliest claimed: 2015-03-12
- Assignees: The Board of Trustees of the University of Illinois
- Applicants: The Board of Trustees of the University of Illinois
- Inventors: Joseph D. Donovan; Soo-Yeun Lee; Youngsoo Lee
- Web page: https://patentgrep.com/patent/US10864281B2

## CPC

- A61K 47/6949: {inclusion complexes, e.g. clathrates, cavitates or fullerenes}
- A23L 33/10: using additives (addition of substantially indigestible substances A23L33/21)
- A23L 33/12: Fatty acids or derivatives thereof
- A23L 33/15: Vitamins
- A23L 33/155: Vitamins A or D
- A23L 33/16: Inorganic salts, minerals or trace elements
- A23L 33/17: Amino acids, peptides or proteins
- A23L 33/40: {Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula}
- A61K 31/07: Retinol compounds, e.g. vitamin A (retinoic acids A61K31/203)
- A61K 31/225: Polycarboxylic acids
- A61K 31/25: with polyoxyalkylated alcohols, e.g. esters of polyethylene glycol
- A61K 31/355: Tocopherols, e.g. vitamin E
- A61K 31/593: 9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/6951: {using cyclodextrin (cyclodextrins used as simple excipients A61K47/40)}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

The invention provides novel formulations comprising a stable inclusion complex of tributyrin and a cyclodextrin. In one particular embodiment, the formulation comprises an oven dried inclusion complex of tributyrin and γ-cyclodextrin that is effective in minimizing or preventing the unpleasant taste and odor of tributyrin, thus making it suitable for oral administration and delivery to the digestive tract and intestines. The invention provides compositions of these inclusion complexes and methods of using them that are advantageous as food, medicinal and other products, where the negative sensory properties of tributyrin can be a liability.

## Claims

### Claim 1

A stable inclusion complex comprising tributyrin and γ-cyclodextrin, wherein the molar ratio of tributyrin to γ-cyclodextrin consists of about 1:1 to about 1:3 and the inclusion complex is olfactorily and gustorialy neutral in comparison to free tributyrin wherein tributyrin is encapsulated by γ-cyclodextrin to form a solid inclusion complex.

### Claim 2 (depends on 1)

The stable inclusion complex of claim 1 wherein the solid inclusion complex is not degraded at forming the solid inclusion complex.

### Claim 3 (depends on 1)

The stable inclusion complex of claim 1 wherein the solid inclusion complex has a water content of about 9% to about 11% by weight.

### Claim 4 (depends on 1)

The stable inclusion complex of claim 1 wherein the solid inclusion complex is a dry product.

### Claim 5 (depends on 4)

The stable inclusion complex of claim 4 wherein the solid inclusion complex has been dried at about 45° C. for at least 3 hours.

### Claim 6

A stable inclusion complex comprising tributyrin and γ-cyclodextrin, wherein the molar ratio of tributyrin to γ-cyclodextrin is about 1:1 to about 1:3 and the inclusion complex is olfactorily and gustorialy neutral in comparison to free tributyrin wherein the inclusion complex is oven dried.

### Claim 7 (depends on 1)

A food additive comprising the inclusion complex of claim 1 and a dietary acceptable supplement.

### Claim 8 (depends on 7)

The food additive of claim 7 further comprising calcium, at least one natural flavor, at least one sweetener, at least one disintegrant, at least one protein, at least one carbohydrate, at least one other mineral, at least one vitamin, or at least one organic acid.

### Claim 9 (depends on 7)

The food additive of claim 7 wherein the supplement comprises an omega-3 fatty acid, Vitamin A, Vitamin D3, Vitamin E, or a combination thereof.

### Claim 10 (depends on 1)

An oral infant formula comprising the inclusion complex of claim 1 and one or more of milk, water, a protein, a carbohydrate or sugar, a mineral, a vitamin, or an edible fat.

### Claim 11 (depends on 1)

A method of preparing the stable inclusion complex according to claim 1, comprising:
a) mixing trubutyrin and γ-cyclodextrin in water to form a first inclusion complex; and
b1) drying the first inclusion complex for a sufficient period of time to form a stable inclusion complex at a temperature that does not degrade the stable inclusion complex; or
b2) drying the first inclusion complex for a sufficient period of time to form a stable inclusion complex that has a moisture content of less than about 11%;
wherein the stable inclusion complex has a taste and odor that is indistinguishable from a γ-cyclodextrin that does not comprise tributyrin.

### Claim 12 (depends on 1)

A method of inhibiting an inflammatory bowel disease or disorder comprising administering a therapeutically effective amount of the stable inclusion complex of claim 1 to a subject in need thereof.

### Claim 13 (depends on 12)

The method of claim 12 wherein the inflammatory bowel disease or disorder comprises ulcerative colitis, Crohn's disease, irritable bowel syndrome, shortened bowel syndrome, or a combination thereof.

### Claim 14 (depends on 1)

A method of inhibiting colon cancer comprising administering a therapeutically effective amount of the stable inclusion complex of claim 1 to a subject in need thereof.

### Claim 15 (depends on 1)

A method of relieving food deficiency comprising administering a therapeutically effective amount of the stable inclusion complex of claim 1 to a subject in need thereof.

### Claim 16 (depends on 15)

The method of claim 15 wherein the therapeutically effective amount is about 12.5 g per day.

### Claim 17 (depends on 1)

The stable inclusion complex of claim 1 wherein the molar ratio of tributyrin to γ-cyclodextrin is 1:2.